+

WO2002006371A2 - Compositions durcissables par radiation et articles durcis - Google Patents

Compositions durcissables par radiation et articles durcis Download PDF

Info

Publication number
WO2002006371A2
WO2002006371A2 PCT/US2001/041273 US0141273W WO0206371A2 WO 2002006371 A2 WO2002006371 A2 WO 2002006371A2 US 0141273 W US0141273 W US 0141273W WO 0206371 A2 WO0206371 A2 WO 0206371A2
Authority
WO
WIPO (PCT)
Prior art keywords
radiation
composition
formula
cured
carbon atoms
Prior art date
Application number
PCT/US2001/041273
Other languages
English (en)
Other versions
WO2002006371A3 (fr
Inventor
David A. Smetana
Joseph V. Koleske
Original Assignee
Suncolor Corporation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Suncolor Corporation filed Critical Suncolor Corporation
Priority to JP2002512271A priority Critical patent/JP2004504427A/ja
Priority to CA 2415707 priority patent/CA2415707A1/fr
Priority to EP01956162A priority patent/EP1303553A2/fr
Priority to AU2001278189A priority patent/AU2001278189A1/en
Publication of WO2002006371A2 publication Critical patent/WO2002006371A2/fr
Publication of WO2002006371A3 publication Critical patent/WO2002006371A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
    • C08K5/0025—Crosslinking or vulcanising agents; including accelerators
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
    • C08F283/10—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polymers containing more than one epoxy radical per molecule
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/061—Polyesters; Polycarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
    • C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
    • C08F290/06—Polymers provided for in subclass C08G
    • C08F290/064—Polymers containing more than one epoxy group per molecule
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
    • H05K3/00—Apparatus or processes for manufacturing printed circuits
    • H05K3/22—Secondary treatment of printed circuits
    • H05K3/28—Applying non-metallic protective coatings
    • H05K3/285—Permanent coating compositions
    • H05K3/287—Photosensitive compositions
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y10T428/252—Glass or ceramic [i.e., fired or glazed clay, cement, etc.] [porcelain, quartz, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y10T428/254—Polymeric or resinous material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/25—Web or sheet containing structurally defined element or component and including a second component containing structurally defined particles
    • Y10T428/259—Silicic material
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/261—In terms of molecular thickness or light wave length
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/26—Web or sheet containing structurally defined element or component, the element or component having a specified physical dimension
    • Y10T428/263—Coating layer not in excess of 5 mils thick or equivalent
    • Y10T428/264—Up to 3 mils
    • Y10T428/265—1 mil or less
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2993—Silicic or refractory material containing [e.g., tungsten oxide, glass, cement, etc.]
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
    • Y10T428/2982—Particulate matter [e.g., sphere, flake, etc.]
    • Y10T428/2991—Coated
    • Y10T428/2998—Coated including synthetic resin or polymer
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31511—Of epoxy ether
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31855—Of addition polymer from unsaturated monomers
    • Y10T428/31935—Ester, halide or nitrile of addition polymer

Definitions

  • This invention relates to radiation-curable compositions and articles
  • compositions may be cured with electron beam radiation
  • UV ultraviolet
  • visible light visible light
  • gamma rays and the like.
  • compositions are based on technology that invokes cure through a free-
  • Electron beam curing is used for compositions based on acrylates and
  • Photocure technology requires the addition of a compound known as
  • the photoinitiator photolyzes, i.e.,
  • compositions as well as clear, thick compositions at
  • U.S. Patent No. 5,453,451 relates to a substantially solvent free
  • liquid, sprayable coating composition including one or more acrylates and
  • one or more photoinitiators that polymerize the composition when exposed
  • U.S. Patent No. 4,721 ,734 relates to photoinitiator
  • U.S. Patent 4,425,287 relates to a process for the production of
  • a pulverulent filler is employed that transmits ultraviolet light so that curing is complete even in the deeper
  • suitable fillers are aluminum oxide hydrate,
  • glass in general is opaque to ultraviolet
  • quartz is typically
  • quartz sand contains impurities
  • Barium sulfate is unsatisfactory in the compositions of
  • the present invention because it is crystalline and has a high specific gravity
  • Talc is unsatisfactory because it is crystalline and also
  • finely disperse silica does not indicate whether it is crystalline or
  • Crystalline silica presents the same
  • compositions and substrates exist, most of them are clear coatings that are
  • invention provides such novel compositions.
  • a radiation-curable composition in a liquid or solid form comprises at least
  • At least one cationic-curable or free-radical curable composition or mixture at least one cationic-curable or free-radical curable composition or mixture
  • transmissible means substantially transparent to
  • transmissible materials comprise certain glasses, quartzes, and other
  • the cationic-curable compositions comprise at least one
  • cycloaliphatic epoxide at least one cation-generating photoinitiator
  • compositions comprise at least one ethylenically-unsaturated compound
  • compositions of the invention are useful as coatings and inks for metal,
  • compositions of this invention can be liquids or
  • solids and comprise at least one solid, non-crystalline, radiation-
  • transmissible material dispersed in at least one cationic-curable or free-
  • the solid, non-crystalline radiation-transmissible materials transmit
  • Such materials can be inorganic or organic.
  • regular crystal lattice i.e., are substantially not arranged in a three-
  • a crystal lattice is a regular pattern of
  • Corning Pyrex ® 7070 potash borosilicates such as Corning 7761 , soda
  • borosilicates such as Corning 7740, uviol glasses, and the like.
  • glasses can be considered to be high viscosity liquids, they are solids as a
  • quartzes also comprise certain non-crystalline quartzes, including amorphous silicas
  • fused quartz is also known as quartz glass.
  • Mixtures of such radiation-transmissible materials can also be used.
  • Suitable radiation-transmissible materials for use in this invention are
  • the solid, non-crystalline, radiation-transmissible materials comprise
  • UV light transmission i.e., substantial transparency
  • a spectrophotometer preferably having at least the accuracy of a
  • UV light transmission percentages increase as the thickness of
  • radiation-transmissible material is preferred, having minimum radiation-
  • D line from about 1 .3 to about 2.0, and preferably from about 1 .42 to
  • the solid, non-crystalline radiation-transmissible materials preferably
  • crystalline radiation-transmissible materials preferably have a specific gravity
  • the solid, non-crystalline radiation-transmissible materials also include
  • the solid, non-crystalline, radiation-transmissible materials can be any solid, non-crystalline, radiation-transmissible materials.
  • Particle sizes may vary widely but typically are from a mean
  • the particles are preferably from about 0.2 micron to about 1 000 microns.
  • the radiation-transmissible materials are non-reactive materials
  • compositions i.e., do not lump or clump together.
  • compositions Furthermore, abrasion resistance is often a desirable
  • compositions of this invention The radiation-transmissible
  • materials preferably have a Mohs hardness from about 4.5 to about 7 and
  • silica radiation-transmissible materials are remarkably stable under atomic and radiation bombardment and are particularly useful in electron
  • compositions in order to optimize the transmission of radiation through the
  • the refractive index of the polymeric or coatings base resins is the refractive index of the polymeric or coatings base resins.
  • transmissible materials can be treated or coated with any substance
  • the radiation-transmissible materials can be any radiation-transmissible materials.
  • the radiation-transmissible materials can be any radiation-transmissible materials.
  • the radiation-transmissible materials can also be dyed in color by any means, and the refractive index (Becke Line) altered by internal dyes or
  • curable compositions of this invention are based on 1 00 parts by
  • ingredients are added to the compositions on a PHR (parts per hundred)
  • curable compositions of this invention are present at from about 2 to about
  • 500 parts preferably from about 5 parts to about 300 parts, and most
  • the physical properties of the radiation-transmissible (such as
  • abrasion resistance, toughness, and insulating resistance may be imparted to the cured ultraviolet-curable composition, potentially improving such
  • the cationic radiation-curable compositions include at least one
  • cycloaliphatic epoxide and preferably one or more polyfunctional
  • cycloaliphatic epoxides Polyfunctional cycloaliphatic epoxides,
  • dimers, trimers, and higher oligomers of epoxides can be present in any one
  • Suitable cycloaliphatic epoxides for purposes of this invention are those
  • the epoxy groups may be internal epoxy groups or terminal
  • epoxy groups as exemplified by the cycloaliphatic epoxides, which are
  • cyclohexane diepoxides which are epoxides having at least one
  • Suitable cycloaliphatic epoxides are the following:
  • R ⁇ through R 9 which independently are hydrogen or linear or
  • branched alkyl radicals generally containing from one to ten carbon atoms
  • particularly desirable compound is that in which R., through R 9 are hydrogen.
  • epoxycyclohexanecarboxylate 3,4-epoxy-6-methyl-cyclohexylmethyl-3,4-
  • Patent No. 2,890, 1 94 Patent No. 2,890, 1 94.
  • R ⁇ through R g are the same as defined for structural Formula I, and
  • R is a valence bond or a linear or branched divalent hydrocarbon radical
  • trimethylene tetramethylene, hexamethylene, 2-ethylhexylene, and the like
  • epoxycyclohexylmethyDadipate bis(3,4-epoxy-6-
  • R, to R 9 independently are hydrogen or linear or branched
  • hydrocarbon radicals containing one to three carbon atoms A particularly preferred hydrocarbon radicals containing one to three carbon atoms.
  • useful epoxide is one in which R, to R 9 are hydrogen and said compound is
  • diepoxide diepoxide, ⁇ -pinene diepoxide; trimethylolpropane mono-, di- and triglycidyl
  • modified cycloaliphatic epoxides such as UvacureTM 1 530,
  • Polyfunctional epoxides provide a high degree of crosslinking and attendant
  • Preferred cycloaliphatic diepoxides include one or more of (a) 3,4-
  • epoxide groups are preferred, minor amounts of up to about 30% or
  • polyfunctional epoxide can be used in the compositions of this invention.
  • suitable monoepoxides are limonene
  • oxetanes such as 3-ethyl-3-hydroxymethyl oxetane and the
  • ⁇ -olefin epoxides such 1 ,2-epoxy hexane, as 1 ,2-epoxy decane, 1 ,2-
  • Preferred monoepoxides include limonene monoepoxide and 3-
  • Monofunctional epoxides typically have
  • glycidyl epoxides may be used, such as
  • compositions of this invention to provide flexibility and toughness to the
  • polyester polyols polycaprolactone polyols, polyether polyols, polyacrylate
  • polyols polyvinyl polyols, polycarbonate polyols, and the like, as well as the
  • caprolactone poly- ⁇ -valerolactone, and other polylactone polyols;
  • polyester polyols such as the polyester adipates and polyester oxalates
  • butyl acrylate such as ethylene glycol, diethylene glycol, butylene
  • triols such as trimethylolpropane
  • polycaprolactone polyols examples include polycaprolactone polyols, poly(propylene oxide) polyols,
  • polypropylene oxide polypropylene oxide
  • Polyols of the above types are well known articles of commerce and widely used in the coatings, inks, adhesives,
  • molecular weight of from about 300 to about 5000, preferably from about
  • poly(tetramethylene oxide) diols having a number-average
  • R is a linear or branched alkane of 3 to 6 carbon atoms, preferably
  • n is an integer of from about 3 to about 25.
  • polyols include poly(oxypropylene-oxyethylene) polyols; however, desirably
  • the oxyethylene content should comprise less than about 40 weight percent
  • the ethylene oxide can be incorporated in any manner
  • incorporated either in internal blocks, as terminal blocks, may be randomly distributed along the polymer chain, or may be randomly distributed in a
  • glycols 1,3-bis(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminols, 1,3-diols, 1,3-diols, 1,3-dioethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-aminoethyl-N-(trimethyl)-2-a
  • more than one polyol can be used in a given formulation provided
  • Polyols are present at from zero to about 1 00, preferably from about
  • compositions can contain minor amounts up to about
  • monohydroxyl functional compounds such as methanol, ethanol, propanol,
  • polycaprolactone polyols and the poly(tetramethylene oxide) polyols are examples of polycaprolactone polyols and the poly(tetramethylene oxide) polyols.
  • poly(oxypropylene-oxyethylene) polyols are usually used for coatings that
  • Particularly useful polyols are the polycaprolactone diols and
  • compositions include those that generate cations and known in the industry
  • M is selected from phosphorous, antimony, arsenic as described in U. S.
  • UVI-6990 commercially available UVI-6990, UVI-6974, UVI-6976, and UVI-6992
  • aromatic iodonium salts of said elements such as diaryliodonium hexafluoroantimonate.
  • ferrocenium salts such as
  • IMACURE ® 261 (CIBA Specialty Chemicals) which can be used alone or in
  • the photoinitiators may be any organic compound that can be used to oxidize the salt to a stronger cationic species.
  • the photoinitiators may be any organic compound that can be used to oxidize the salt to a stronger cationic species.
  • the photoinitiators may be any organic compound that can be used to oxidize the salt to a stronger cationic species.
  • the photoinitiators may be any organic compound that can be used to oxidize the salt to a stronger cationic species.
  • the photoinitiators are present from about 0.03 to about 25 parts,
  • photosensitizer may be added to the photoinitiator in the photocurable
  • Aryl sulfonium salts can be
  • Preferred photosensitizers include substituted xanthone
  • compositions optionally can contain acrylates and related compounds.
  • acrylates in this document is meant to encompass both acrylates and
  • Suitable acrylates for use in the cation-curable formulations include
  • esters of acrylic and methacrylic acid having the general structural Formula
  • R is hydrogen or methyl and R' is hydrogen; a linear or branched
  • alkyl containing one to 1 0 carbon atoms, preferably one to six carbon
  • n is from 3 to 8
  • m is from 1 to ten, preferably from 1 to 3, and most
  • R 10 -O-C(O)-C(R) CH 2 wherein R 10 is linear or branched alkyl
  • R is hydrogen or methyl; pentaerythritol mono-, di-, tri-, and tetra-
  • alkoxylated trimethylolpropane acrylate wherein the alkoxy group has 2 to
  • acrylates are methyl, ethyl, propyl, butyl,
  • caprolactone derivatives i.e., reaction products of 2-hydroxyethyl acrylate
  • poly(ethylene glycol) diacrylates 2,2-dimethyl-3-hydroxypropyI-2,2-
  • silica organosols of acrylates such as the products commercially available
  • oligomeric acrylates such as the commercially available acrylates
  • n is from 1 to about 30 or more preferably from about 1 0;
  • polyisocyanates and optionally glycols, and known in the industry as
  • acrylates are present in an amount of up to about 50 parts, preferably up to about 35 parts by weight per 1 00 parts by weight of cycloaliphatic
  • Preferred acrylates include one or more of (a) ⁇ -caprolactone
  • alkyl group has 2 to about 4 carbon atoms; (b) alkoxylated
  • the cationic radiation-curable compositions can also contain
  • ethers are acrolein dimer, acrolein tetramer, 1 ,4-cyclohexanedimethanol
  • divinyl ether triethylene glycol divinyl ether, tripropylene glycol divinyl
  • the vinyl ethers are present in an amount of less
  • compositions of the invention can be any suitable cationic radiation-curable compositions of the invention.
  • vinyl acetate vinyl pyrrolidone, vinyl caprolactam, vinyl esters, and the like.
  • compositions of the invention may be any suitable cationic radiation-curable compositions of the invention.
  • pigments are present in an amount of from about 0.005 parts to about
  • the free-radical-curable compositions typically include at least one
  • acrylate preferably two or more acrylates, and at least one free-radical-
  • the amount of photoinitiator can be
  • Suitable acrylates include those described
  • the free-radical-curable compositions can also include
  • curable formulations include benzophenone, 4,4'-bis(N-ethyl-N-
  • pivaloyldiphenylphosphine oxide 2,6-dichlorobenzoyldiphenylphospine
  • alpha-aminoalkylphenones such as 2-benzyl-2-dimethylamino-1 -
  • acylphosphine oxides such as the monoacylphosphine
  • Preferred free-radical-generating photoinitiators include benzophenone, 2,2-
  • photoinitiators that generate free radicals during the photolysis process can be any photoinitiators that generate free radicals during the photolysis process.
  • the photoinitiators for the free-radical curable compositions are used in an
  • free radical-generating photoinitiators such as benzophenone, benzils, and
  • a synergist is a compound that contains a carbon atom with at
  • synergists are the tertiary amines, amines, and ureas which
  • synergists include triethylamine and N-
  • initiating free radicals can decrease the oxygen inhibition difficulty that
  • adhesion promoters to the compositions of
  • SR901 2 (a trifunctional acrylate monomer), SR901 6 (a metallic diacrylate),
  • SR9050 (a monofunctional acid ester)
  • SR9051 (a trifunctional acid ester)
  • SR9052 (a trifunctional acid ester), and the like.
  • compositions may contain a fluorescent dye to act as a means of marking
  • UV light ultraviolet light
  • fluorescent dyes are CalcafluorTM
  • the fluorescent dye is
  • the preferred amount from about 0.01 part to about 0.1 5 part by weight
  • dyestuffs optionally may be added to the cationic and free-radical curable
  • coatings of the invention to improve the color or hide yellowing in coatings
  • Visible light photoinitiators include compounds such as D,L-
  • camphorquinone such as Rose Bengal, fluorones, and the
  • the photocurable compositions of the invention may also contain
  • ingredients such as one or more surfactants, flow and leveling agents,
  • defoamers fumed silicas, fillers, alumina, silicone oils, slip agents, viscosity
  • polymers such as the vinyl chloride/vinyl acetate copolymers; functional
  • vinyl chloride/vinyl acetate terpolymers such as vinyl chloride/vinyl
  • terpolymers and the like; acrylate copolymers and terpolymers such as
  • thickeners includes the new associative
  • the coating compositions optionally also may contain or be dissolved
  • the coating industry can be used at a concentration of less than about 1 00
  • Suitable solvents include acetone, methyl ethyl ketone, amyl ketone, amyl
  • photosensitizer is used and is incorporated into the curable compositions of
  • curable compositions of the invention can be applied to a suitable substrate
  • compositions occurs on exposure of the compositions to actinic radiation at a wavelength
  • Exposure to the energy source may be from less than about one second to
  • the particular radiation source the distance of composition from the
  • curable compositions is often what may be called a triggered reaction.
  • sealant, composite, or other article allows clear, thick clear, and thick
  • photoinitiator radiation source intensity, distance from the radiation source
  • Photopolymerization is carried out by exposing the radiation-curable
  • compositions such as films, coatings, inks, adhesives, sealants, or
  • ultraviolet light and visible light preferably having a wavelength from about
  • photoinitiators ultraviolet light may be used alone and with others visible
  • cure of the free-radical curable compositions of this invention is ultraviolet
  • electron beam radiation can be used to supplement or
  • Such electron beam radiation can reduce or
  • radiation source or a thermal source may be used to supplement radiation
  • compositions of the invention may have very
  • compositions of this invention also are cured as composite materials.
  • the cured compositions of this invention also are
  • the radiation-curable thermoplastic material in a particular embodiment of the invention, the radiation-curable thermoplastic material, the radiation-curable thermoplastic material, and the radiation-curable thermoplastic material.
  • compositions of the invention can be combined with various structural elements
  • the structural fibers useful with the compositions are carbon, graphite, glass
  • optical fibers silicon carbide, polybenzothiazole, alumina, titania,
  • the fibers can be used in various ways.
  • Such composites have a variety of end
  • fibers may be coated in single filament or multi-filament form. Pigmented or
  • radiation-curable compositions of the invention include photoresists, solder
  • Fiber-glass-composite printed-circuit assemblies and similar
  • composites that are made of ceramic materials can have the cationic-cured
  • curable compositions are made into solid particles by using a mixture of
  • fluid energy milling to form powders or can be spray dried from a melt or
  • powders can be applied by electrostatic spray or fluidized-bed methods.
  • the coating is periodically
  • the test is performed immediately after the coating leaves the light source.
  • the coating is disrupted, i.e., tears, twists, wrinkles, or mars, the coating is disrupted, i.e., tears, twists, wrinkles, or mars, the coating is disrupted, i.e., tears, twists, wrinkles, or mars, the coating is disrupted, i.e., tears, twists, wrinkles, or mars, the coating is disrupted, i.e., tears, twists, wrinkles, or mars, the coating is
  • test usually is applied immediately after removing
  • Sartomer Co., Inc. as CN 981 , CN 968, CN 980 or equivalent.
  • Defoamer I A polysiloxane defoamer commercially available from BYK-
  • Dye I Dye NLE 2591 21 , a blue dyestuff commercially available from BASF
  • Dye II A fluorescent dye of unknown composition commercially available
  • Epoxide I 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate
  • Epoxide II Limonene diepoxide, an epoxide diluent, and commercially
  • Epoxide III 3,4-epoxycyclohexylmethyl-3,4-epoxycyclohexane carboxylate
  • Epoxide IV Bis-(3,4-epoxycyclohexyl)adipate, commercially available from
  • Filler I Hydrated alumina (also called aluminum oxide trihydrate), a white,
  • Photoinitiator I A diaryliodonium hexafluoroantimonate salt in a solvent
  • Photoinitiator II Mixed arylsulfonium hexafluoroantimonate salts as a
  • Photoinitiator III Oligo(2-hydroxy-2-methyl-1 ,4-(1 -
  • Photosensitizer I Isopropyl thioxanthone, a photosensitizer that functions
  • Pigment I A 50% by weight dispersion of titanium dioxide in Cyracure ®
  • Pigment II Exterior Mearlin Micro White, commercially available from
  • Pigment III A 20% by weight dispersion of carbon black in Cyracure ®
  • Resin UVR-61 10, and commercially available from Penn Color, Inc. as
  • Pigment IV Finely divided titanium dioxide pigment, commercially available
  • Pigment V Finely divided carbon black pigment solids, commercially
  • Polyol I A trifunctional poly- ⁇ -caprolactone polyol with an average
  • Polyol II A trifunctional poly- ⁇ -caprolactone polyol with ' an average molecular weight of about 540, and commercially available from Union
  • Polyol III A difunctional poly(tetramethylene oxide) polyol with an average
  • Surfactant I SilwetTM L-7604, commercially available from Witco Corp.
  • UV Source I A synthetic ultraviolet light source consisting of a gallium-
  • microwave powered curing unit equipped with a conveyer
  • UV Source II A synthetic ultraviolet light source consisting of a medium-
  • UV Source III A synthetic ultraviolet light source consisting of an iron-
  • doped arc lamp with an output of 500 watt/inch, located in a curing unit
  • UVT-1 A radiation-transmissible material that is a finely-divided, non-
  • crystalline, f used-quartz powder with a particle size of less than 1 0 microns and ranging in size from about 0.1 microns to about 1 0 microns. It has an
  • ultraviolet light transmittance 90 % or more for radiation having a
  • UVT-2 A radiation-transmissible material comprised of finely divided
  • borosilicate glass spheres with a particle size of less than 20 microns and
  • UVT-3 A radiation-transmissible material that is a finely divided, fused
  • UVT-4 A radiation-transmissible material comprised of finely divided
  • borosilicate glass spheres with a particle size of less than 74 microns and ranging in size from about 20 micron to about 74 microns. It has an
  • Coating were prepared by placing the ingredients for the cationic wood
  • substrate was sanded lightly using 20 strokes with 1 80 grit sandpaper.
  • the coatings were cured either using natural sunlight, which has a high ultraviolet light content, or with UV Source I.
  • wet thickness is essentially the same as cured thickness.
  • Example 1 which contained the radiation-
  • Cationic UV Cure 1 997, state on p. 1 9 that cure rate is proportional to cationic photoinitiator concentration, and on p. 22 that cure rate is
  • the white coating formulation was

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Dental Preparations (AREA)
  • Inks, Pencil-Leads, Or Crayons (AREA)

Abstract

L'invention concerne une composition durcissable par radiation sous forme liquide ou solide. Cette composition comprend au moins un matériau solide, non cristallin, transmissible par radiation, dispersé dans au moins une composition durcissable par cations ou durcissable par radicaux libres ou dans un mélange desdites compositions. Les matériaux solides, non cristallins, transmissibles par radiation comprennent des verres et d'autres matériaux appropriés qui transmettent (c'est-à-dire, qui sont transparents à) au moins environ 40 % de radiation à une longueur d'ondes comprise entre environ 180 et environ 600 nanomètres. Les compositions durcissables par cations comprennent au moins une époxyde cycloaliphatique, au moins un polyol et au moins un photo-initiateur générateur de cations. Les compositions durcissables par radicaux libres comprennent au moins un composé non saturé en éthylène et au moins un photo-initiateur générateur de radicaux libres à moins qu'on ne fasse appel au durcissement par faisceau d'électrons, auquel cas la quantité de photo-initiateur peut être réduite, voire même éliminée. Les formes solides des compositions durcissables par radiation selon l'invention conviennent comme poudres de revêtement pour revêtir des objets décoratifs et fonctionnels, lesquels poudres sont destinées à être durcies par un processus de flux de réchauffage suivi d'une radioexposition. Les compositions durcies selon l'invention conviennent comme revêtements et comme encres pour du métal, du papier, des plastiques, du verre, de la céramique et du bois, en tant qu'adhésifs, qu'agents de scellement et que matériaux composites et autres articles. Les compositions durcies selon l'invention sont également utiles dans des applications biomédicales et dentaires, notamment des dispositifs de prothèse tels que des dentiers; des revêtements, des obturations et des chapes dentaires; et des dispositifs analogues.
PCT/US2001/041273 2000-07-13 2001-07-05 Compositions durcissables par radiation et articles durcis WO2002006371A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2002512271A JP2004504427A (ja) 2000-07-13 2001-07-05 放射線硬化性組成物および硬化品
CA 2415707 CA2415707A1 (fr) 2000-07-13 2001-07-05 Compositions durcissables par radiation et articles durcis
EP01956162A EP1303553A2 (fr) 2000-07-13 2001-07-05 Compositions durcissables par radiation et articles durcis
AU2001278189A AU2001278189A1 (en) 2000-07-13 2001-07-05 Radiation-curable compositions and cured articles

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US09/616,201 US6350792B1 (en) 2000-07-13 2000-07-13 Radiation-curable compositions and cured articles
US09/616,201 2000-07-13

Publications (2)

Publication Number Publication Date
WO2002006371A2 true WO2002006371A2 (fr) 2002-01-24
WO2002006371A3 WO2002006371A3 (fr) 2002-07-25

Family

ID=24468432

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2001/041273 WO2002006371A2 (fr) 2000-07-13 2001-07-05 Compositions durcissables par radiation et articles durcis

Country Status (6)

Country Link
US (2) US6350792B1 (fr)
EP (1) EP1303553A2 (fr)
JP (1) JP2004504427A (fr)
AU (1) AU2001278189A1 (fr)
CA (1) CA2415707A1 (fr)
WO (1) WO2002006371A2 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004352980A (ja) * 2003-05-07 2004-12-16 Mitsui Chemicals Inc 光カチオン重合性樹脂組成物及び光ディスク表面保護用材料
JP2005054127A (ja) * 2003-08-07 2005-03-03 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005060463A (ja) * 2003-08-08 2005-03-10 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005060462A (ja) * 2003-08-08 2005-03-10 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005112936A (ja) * 2003-10-06 2005-04-28 Konica Minolta Medical & Graphic Inc 活性エネルギー線硬化型インクジェットインク及び印刷物
JP2006070164A (ja) * 2004-09-02 2006-03-16 Toray Ind Inc 可視光硬化性樹脂組成物
US7709553B2 (en) 2003-05-07 2010-05-04 Mitsui Chemicals, Inc. Photo cation polymerizable resin composition and surface protective material for optical disk
WO2010071952A1 (fr) 2008-12-22 2010-07-01 Technosolutions Assessoria Ltda Procédé d'impression flexographique avec procédé humide
CN104487221A (zh) * 2012-03-01 2015-04-01 纳斯达克有限公司 阳离子可聚合组合物及其使用方法

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3023301A (en) * 2000-02-08 2001-08-20 Vantico Ag Liquid, radiation-curable composition, especially for stereolithography
GB0007731D0 (en) * 2000-03-31 2000-05-17 Altro Ltd Coloured silicon carbide
US6485306B1 (en) * 2001-07-10 2002-11-26 Aiptek International Inc. Locus-recordable portable handwriting device
US6579914B1 (en) * 2000-07-14 2003-06-17 Alcatel Coating compositions for optical waveguides and optical waveguides coated therewith
US6737467B1 (en) * 2000-11-21 2004-05-18 E. I. Du Pont De Nemours And Company Low gloss powder coatings
US6784222B2 (en) * 2001-03-07 2004-08-31 Frank David Zychowski 100% solids radiation curable conductive primer
US6835679B2 (en) * 2001-12-27 2004-12-28 Continuum Dynamics, Inc. Lossy fiber UV curing method and apparatus
JP3886813B2 (ja) * 2002-01-24 2007-02-28 富士通株式会社 研磨方法
US7309732B1 (en) 2003-04-21 2007-12-18 Henkel Corporation UV and UV/moisture dual curable compositions with improved cure through volume
KR20030087234A (ko) * 2002-05-08 2003-11-14 박홍수 아크릴계 4원 공중합 수지와 그 제조방법 및 이를 주재로하는자동차용 하이솔리드 도료
US6964722B2 (en) * 2002-08-07 2005-11-15 Trio Industries Holdings, L.L.C. Method for producing a wood substrate having an image on at least one surface
US6777027B2 (en) * 2002-10-08 2004-08-17 Rohm And Haas Company Coating powders for smooth, low gloss finishes, and powder coatings formed therefrom
US6734409B1 (en) 2002-10-31 2004-05-11 Corning Incorporated Microwave assisted bonding method and joint
NL1024722C2 (nl) * 2002-11-07 2005-12-23 Corning Inc Laag uitgassend rubberachtig polymeermateriaal dat hardbaar is door een licht- of elektronenbundel, alsmede de bereiding en het gebruik daarvan.
WO2005021634A2 (fr) * 2003-02-20 2005-03-10 Texas Research International, Inc. Compositions a sechage ultraviolet destinees a la reparation de composites
US9058912B2 (en) 2003-04-04 2015-06-16 Toray Industries, Inc. Paste composition and dielectric composition using the same
WO2004090912A1 (fr) * 2003-04-04 2004-10-21 Toray Industries, Inc. Composition de pate et composition dielectrique la contenant
KR100500453B1 (ko) * 2003-06-23 2005-07-12 삼성전자주식회사 이중층 레지스트막의 하부 레지스트 층의 형성방법
US20050148681A1 (en) * 2003-10-02 2005-07-07 Schoen Catherine A. Photoinitiator and ink
JP2005113043A (ja) * 2003-10-09 2005-04-28 Konica Minolta Medical & Graphic Inc 活性光線硬化型インク組成物、画像形成方法及びインクジェット記録装置
JP2005120201A (ja) * 2003-10-16 2005-05-12 Konica Minolta Medical & Graphic Inc 活性光線硬化型インクジェットインク組成物とそれを用いた画像形成方法及びインクジェット記録装置
JP2005154679A (ja) * 2003-11-28 2005-06-16 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物及び活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
US7250238B2 (en) * 2003-12-23 2007-07-31 Xerox Corporation Toners and processes thereof
US20050159521A1 (en) * 2004-01-20 2005-07-21 Brown Donald A. Reversible adhesive
JP4396344B2 (ja) * 2004-03-22 2010-01-13 コニカミノルタエムジー株式会社 インクジェットインクとそれを用いた画像形成方法及びラインヘッド記録方式のインクジェット記録装置
KR101125678B1 (ko) 2004-02-06 2012-03-28 롬 앤드 하스 일렉트로닉 머트어리얼즈, 엘.엘.씨. 개선된 이미지화 조성물 및 방법
US7977026B2 (en) * 2004-02-06 2011-07-12 Rohm And Haas Electronic Materials Llc Imaging methods
US20050175941A1 (en) 2004-02-06 2005-08-11 Rohm And Hass Electronic Materials, L.L.C. Imaging composition and method
US7270932B2 (en) * 2004-02-06 2007-09-18 Rohm And Haas Electronic Materials Llc Imaging composition and method
US7144676B2 (en) 2004-02-06 2006-12-05 Rohm And Haas Electronic Materials Llc Imaging compositions and methods
DE102004008365A1 (de) * 2004-02-20 2005-09-08 Altana Electrical Insulation Gmbh Verfahren zur Herstellung von beschichteten elektrischen Drähten
US20050217572A1 (en) * 2004-03-30 2005-10-06 Ming-Wan Young Ultraviolet particle coating systems and processes
US7510746B2 (en) * 2004-06-04 2009-03-31 E.I. Du Pont De Nemours And Company Process for production of multilayer coating including curing clear-coat composition with high-energy radiation
JP2006008791A (ja) * 2004-06-24 2006-01-12 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
US7208257B2 (en) * 2004-06-25 2007-04-24 Xerox Corporation Electron beam curable toners and processes thereof
US7435453B2 (en) * 2004-08-04 2008-10-14 Valspar Sourcing, Inc. Method of finishing veneer surface of veneered wood product by application and curing of UV-curable coating layers having cationically and free-radically polymerizable moieties
US7134872B2 (en) * 2004-09-02 2006-11-14 Norbert Abels Colored orthodontic brackets
US20060058415A1 (en) * 2004-09-14 2006-03-16 Arthur Samuel D Materials leading to improved dental composites and dental composites made therefrom
US7423073B2 (en) * 2004-11-23 2008-09-09 Lexmark International, Inc. Radiation curable compositions having improved flexibility
US7838570B2 (en) * 2005-01-14 2010-11-23 Xerox Corporation Radiation curable inks
KR100619770B1 (ko) 2005-01-26 2006-09-11 주식회사 씨씨텍 광 및 열 경화형 액정디스플레이 패널 봉지제
US7335402B2 (en) * 2005-03-09 2008-02-26 Ppg Industries Ohio, Inc. Radiation curable putty compositions and methods for refinishing a substrate using such compositions
US20060222829A1 (en) * 2005-04-01 2006-10-05 E Dean Roy Substrates coated with coating systems that include a treatment layer
WO2006116032A2 (fr) * 2005-04-21 2006-11-02 Ndsu Research Foundation Films polymeres durcissant par exposition a un rayonnement, presentant des proprietes d'ablation au laser ameliorees, et sensibilisateurs, destines a ces films, durcissant par exposition a un rayonnement
SE0501028L (sv) * 2005-05-04 2006-11-05 Perstorp Specialty Chem Ab Hybrid radiation curable composition and use thereof
US7691557B2 (en) * 2005-06-29 2010-04-06 Dymax Corporation Polymerizable composition exhibiting permanent color change as cure indicator
US20070026089A1 (en) * 2005-07-29 2007-02-01 Trendon Touch Technology Corp. Touch screen with bacteria inhibition layer and manufacturing method thereof
GB0516515D0 (en) * 2005-08-11 2005-09-21 Sun Chemical Bv A jet ink and ink jet printing process
US20070035604A1 (en) * 2005-08-12 2007-02-15 Jang James M Cationic ink formulations
DE102005040126A1 (de) * 2005-08-25 2007-03-01 Altana Electrical Insulation Gmbh Überzugsmasse
US7989517B2 (en) * 2005-11-28 2011-08-02 Konica Minolta Medical & Graphic, Inc. Actinic ray curable composition, actinic ray curable ink, and image formation process employing the same
JP4916186B2 (ja) * 2006-02-24 2012-04-11 株式会社トクヤマ 歯科用接着材
CN101415769A (zh) * 2006-03-29 2009-04-22 国家淀粉及化学投资控股公司 辐射固化橡胶粘合剂/密封剂
EP2001965B1 (fr) 2006-03-31 2016-10-05 SDC Technologies, Inc. Compositions de revetement, articles et procedes de revetement d'articles
US7611352B2 (en) * 2006-08-31 2009-11-03 Ultradent Products, Inc. Lifestyle bracket system having interchangeable ligation covers
WO2008045968A2 (fr) * 2006-10-10 2008-04-17 Adco Products, Inc. Composition de matériau d'étanchéité durcissable par rayonnement
ES2688777T3 (es) 2006-10-12 2018-11-06 Suncolor Corporation Composiciones poliméricas
KR100773634B1 (ko) * 2006-10-26 2007-11-05 제일모직주식회사 아크릴 바인더 수지조성물를 포함하는 광경화형 점착조성물및 이를 이용한 점착테이프
JP2008158310A (ja) * 2006-12-25 2008-07-10 Nitto Denko Corp 積層体、液晶パネル、および液晶表示装置
US7568251B2 (en) 2006-12-28 2009-08-04 Kimberly-Clark Worldwide, Inc. Process for dyeing a textile web
US8182552B2 (en) 2006-12-28 2012-05-22 Kimberly-Clark Worldwide, Inc. Process for dyeing a textile web
US7674300B2 (en) * 2006-12-28 2010-03-09 Kimberly-Clark Worldwide, Inc. Process for dyeing a textile web
US20080156427A1 (en) * 2006-12-28 2008-07-03 Kimberly-Clark Worldwide, Inc. Process For Bonding Substrates With Improved Microwave Absorbing Compositions
US7740666B2 (en) 2006-12-28 2010-06-22 Kimberly-Clark Worldwide, Inc. Process for dyeing a textile web
TWI374922B (en) * 2006-12-29 2012-10-21 Eternal Chemical Co Ltd Anti-uv coating composition and the use thereof
US8529775B2 (en) * 2007-02-20 2013-09-10 Revolaze, LLC Decorative products created by lazing graphics and patterns directly on substrates with painted surfaces
US20080216704A1 (en) * 2007-03-09 2008-09-11 Fisher Controls International Llc Conformal Coating
JP4601009B2 (ja) * 2007-03-30 2010-12-22 富士フイルム株式会社 インクジェット記録用インクセット及びインクジェット記録方法
KR101721254B1 (ko) * 2007-04-13 2017-03-29 3디 시스템즈 인코오퍼레이티드 이중 광개시제, 광경화성 조성물, 그것의 용도 및 3차원 물품의 제조방법
US20090004579A1 (en) * 2007-06-27 2009-01-01 Dsm Ip Assets B.V. Clear and colorless three-dimensional articles made via stereolithography and method of making said articles
US8574696B2 (en) * 2007-07-31 2013-11-05 Hewlett-Packard Development Company, L.P. Electronic device housing assembly
DE102007063698B4 (de) * 2007-09-13 2010-10-28 Carl Zeiss Vision Gmbh Optisches Bauelement mit Oberflächenbeschichtung
US8632613B2 (en) 2007-12-27 2014-01-21 Kimberly-Clark Worldwide, Inc. Process for applying one or more treatment agents to a textile web
JP5258723B2 (ja) * 2008-09-24 2013-08-07 積水化学工業株式会社 電子部品用接着剤及び電子部品積層体
JP5727455B2 (ja) 2009-04-03 2015-06-03 ウルトラデント プロダクツ インコーポレイテッド 協調的な金属およびセラミック製歯列矯正用ブラケットシステム
US20110159225A1 (en) * 2009-12-31 2011-06-30 Bostik, Inc. High Performance Foam Adhesive Tape
US9248468B2 (en) 2010-01-15 2016-02-02 Texas Research International, Inc. Ultraviolet light curing compositions for composite repair
CN103080181B (zh) * 2010-06-28 2017-04-12 蓝立方知识产权有限责任公司 可固化树脂组合物
WO2012039379A1 (fr) * 2010-09-22 2012-03-29 積水化学工業株式会社 Composition durcissable pour jet d'encre et procédé de fabrication d'un composant électronique
US20140255714A1 (en) * 2011-10-19 2014-09-11 Dic Corporation Active-energy-ray-curable resin composition, adhesive, and laminate film
KR101971758B1 (ko) * 2012-03-13 2019-04-23 주식회사 다이셀 감광성 수지 조성물 및 그의 경화물, 및 광학 부품
US8691915B2 (en) 2012-04-23 2014-04-08 Sabic Innovative Plastics Ip B.V. Copolymers and polymer blends having improved refractive indices
US9114282B2 (en) * 2012-05-30 2015-08-25 Nike, Inc. Game ball or other article of sports equipment printed with visible light-curable ink and method
KR20130139134A (ko) 2012-06-12 2013-12-20 제일모직주식회사 접착제 조성물, 이를 이용한 편광판, 그 제조 방법 및 이를 포함하는 광학 부재
US20140357425A1 (en) * 2013-05-31 2014-12-04 Nike, Inc. Golf ball with visible light-cured coating and method
EP3271429B1 (fr) * 2015-03-20 2020-05-06 Blue Cube IP LLC Compositions durcissables
US20170210936A1 (en) * 2016-01-25 2017-07-27 Achiewell, LLC Powder coatings for heat sensitive substrates
US10574014B2 (en) * 2017-03-27 2020-02-25 Aptiv Technologies Limited Method for sealing electric terminal assembly
WO2019118690A1 (fr) * 2017-12-14 2019-06-20 Garrison Dental Solutions, Llc Lumière de durcissement avec capteur de rétroaction intégré
US11267913B2 (en) 2018-02-14 2022-03-08 Mighty Buildings, Inc. 3D printed material, structure and method for making the same
JP7024529B2 (ja) * 2018-03-16 2022-02-24 株式会社リコー 硬化型組成物、硬化物、硬化物の製造方法及び硬化物の製造装置
WO2021151707A1 (fr) * 2020-01-27 2021-08-05 Abb Power Grids Switzerland Ag Époxy photodurcissable pour composants électriques
EP4082677A4 (fr) * 2020-01-30 2024-01-24 Toray Industries, Inc. Agent de revêtement, matériau de base intermédiaire de type feuille, film de résine photodurcissable, intermédiaire de matériau composite renforcé de fibres, matériau composite renforcé de fibres, procédé de production d'intermédiaire de matériau composite renforcé de fibres, et procédé de production de matériau composite renforcé par des fibres
CA3182234A1 (fr) * 2020-06-10 2021-12-16 Gregory ELLSON Materiaux pour polymerisation par ouverture de cycle cationique photo-initiee et utilisations associees
BR102021021638A2 (pt) * 2021-10-28 2023-05-09 Wekoamérica Latina Equipamentos Industriais Ltda. Composição de aditivo em pó para cura uv, processo para preparar dita composição, processo de preparação de uma resina, tinta ou verniz em pó curável por radiação uv, resina, tinta ou verniz em pó curável por uv e uso de dita composição
JP2023082922A (ja) * 2021-12-03 2023-06-15 大成化工株式会社 スクイズ容器

Family Cites Families (39)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2750395A (en) 1954-01-05 1956-06-12 Union Carbide & Carbon Corp Diepoxides
US2890194A (en) 1956-05-24 1959-06-09 Union Carbide Corp Compositions of epoxides and polycarboxylic acid compounds
US3318822A (en) 1959-07-21 1967-05-09 Ciba Ltd Epoxidized hydroaromatic acetals
ES305034A1 (es) 1963-10-18 1965-04-01 Ciba Geigy Procedimiento para endurecer compuestos poliepoxidos cicloalifaticos
US3708296A (en) 1968-08-20 1973-01-02 American Can Co Photopolymerization of epoxy monomers
US3586616A (en) 1969-03-14 1971-06-22 Minnesota Mining & Mfg Bis(perfluoroalkylsulfonyl)methane metal salts in cationic polymerization
US4058400A (en) 1974-05-02 1977-11-15 General Electric Company Cationically polymerizable compositions containing group VIa onium salts
GB1512982A (en) 1974-05-02 1978-06-01 Gen Electric Salts
US4161478A (en) 1974-05-02 1979-07-17 General Electric Company Photoinitiators
JPS604640B2 (ja) 1975-07-30 1985-02-05 ソニー株式会社 擬似頭
US4256828A (en) 1975-09-02 1981-03-17 Minnesota Mining And Manufacturing Company Photocopolymerizable compositions based on epoxy and hydroxyl-containing organic materials
DE2722264C2 (de) 1977-05-17 1984-06-28 Merck Patent Gmbh, 6100 Darmstadt Verwendung von substituierten Oxyalkylphenonen als Photosensibilisatoren
CA1109580A (fr) * 1977-11-03 1981-09-22 Kohtaro Nagasawa Resines radio-curables
CH632667A5 (de) * 1978-01-03 1982-10-29 Espe Pharm Praep Opakes, durch uv-licht polymerisierbares zahnfuellmaterial.
US4231951A (en) 1978-02-08 1980-11-04 Minnesota Mining And Manufacturing Company Complex salt photoinitiator
US4223067A (en) * 1978-03-27 1980-09-16 Minnesota Mining And Manufacturing Company Foam-like pressure-sensitive adhesive tape
US4227978A (en) * 1979-06-27 1980-10-14 Minnesota Mining And Manufacturing Company Photohardenable composition
DE2931737A1 (de) 1979-08-04 1981-02-26 Basf Ag Verfahren zur herstellung von formkoerpern aus ungesaettigten polyesterharzen
DE3172366D1 (en) * 1980-12-03 1985-10-24 Ici Plc Dental compositions
US4683287A (en) 1982-11-02 1987-07-28 Union Carbide Corporation Compositions containing a reactive monomer derived from a lactone
US4512340A (en) 1983-02-22 1985-04-23 Johnson & Johnson Products, Inc. Visible light cured orthopedic polymer casts
US4603158A (en) * 1984-09-28 1986-07-29 Battelle Development Corporation Optically transparent elastomers
US4931347A (en) * 1988-09-19 1990-06-05 Nalco Chemical Company Translucent pressure-sensitive adhesive systems
ATE146305T1 (de) * 1989-03-08 1996-12-15 Siemens Ag Tropfenabdeckmassen für elektrische und elektronische bauelemente
US5019745A (en) 1989-08-24 1991-05-28 Rca Licensing Corp. UV-curable adhesive attachment means and method for a cathode-ray tube-yoke combination
US5667934A (en) * 1990-10-09 1997-09-16 International Business Machines Corporation Thermally stable photoimaging composition
WO1992020719A1 (fr) 1991-05-15 1992-11-26 Sokol Andrew A Composition de finition polymerisable par la lumiere ultraviolette, et procede d'utilisation de ladite composition
JPH0586149A (ja) * 1991-09-30 1993-04-06 I C I Japan Kk 光立体成形用樹脂組成物並びに立体成形体の形成方法
DE4133290A1 (de) * 1991-10-08 1993-04-15 Herberts Gmbh Verfahren zur herstellung von mehrschichtlackierungen unter verwendung von radikalisch und/oder kationisch polymerisierbaren klarlacken
US5252694A (en) * 1992-01-22 1993-10-12 Minnesota Mining And Manufacturing Company Energy-polymerization adhesive, coating, film and process for making the same
TW269017B (fr) * 1992-12-21 1996-01-21 Ciba Geigy Ag
US5384339A (en) * 1993-03-09 1995-01-24 Starkey; Donn R. Epoxy based balancing compound and method for balancing a rotor utilizing an ultraviolet-curable epoxy resin composition
DE4335204C1 (de) 1993-10-15 1995-04-06 Jenaer Glaswerk Gmbh Reduzierend erschmolzenes Borosilikatglas mit hoher Transmission im UV-Bereich und guter hydrolytischer Beständigkeit und seine Verwendung
US5554666A (en) * 1995-02-24 1996-09-10 Sunrez Corporation Photocurable compositions
JP3276833B2 (ja) * 1995-12-13 2002-04-22 太陽インキ製造株式会社 光硬化性・熱硬化性艶消しレジストインキ組成物
JP3626275B2 (ja) * 1996-04-09 2005-03-02 Ｊｓｒ株式会社 光硬化性樹脂組成物
US5948922A (en) * 1997-02-20 1999-09-07 Cornell Research Foundation, Inc. Compounds with substituted cyclic hydrocarbon moieties linked by secondary or tertiary oxycarbonyl containing moiety providing reworkable cured thermosets
DE19750147A1 (de) * 1997-11-12 1999-05-27 Siemens Ag Einkomponenten-Epoxidharz zur Abdeckung von elektronischen Bauelementen
JP2000119373A (ja) * 1998-10-13 2000-04-25 Toppan Printing Co Ltd 絶縁性樹脂組成物およびそれを使用した多層プリント配線板

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2004352980A (ja) * 2003-05-07 2004-12-16 Mitsui Chemicals Inc 光カチオン重合性樹脂組成物及び光ディスク表面保護用材料
US7709553B2 (en) 2003-05-07 2010-05-04 Mitsui Chemicals, Inc. Photo cation polymerizable resin composition and surface protective material for optical disk
JP2005054127A (ja) * 2003-08-07 2005-03-03 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005060463A (ja) * 2003-08-08 2005-03-10 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005060462A (ja) * 2003-08-08 2005-03-10 Konica Minolta Medical & Graphic Inc 活性光線硬化型組成物、活性光線硬化型インク、それを用いた画像形成方法及びインクジェット記録装置
JP2005112936A (ja) * 2003-10-06 2005-04-28 Konica Minolta Medical & Graphic Inc 活性エネルギー線硬化型インクジェットインク及び印刷物
JP2006070164A (ja) * 2004-09-02 2006-03-16 Toray Ind Inc 可視光硬化性樹脂組成物
WO2010071952A1 (fr) 2008-12-22 2010-07-01 Technosolutions Assessoria Ltda Procédé d'impression flexographique avec procédé humide
CN104487221A (zh) * 2012-03-01 2015-04-01 纳斯达克有限公司 阳离子可聚合组合物及其使用方法
US10960600B2 (en) 2012-03-01 2021-03-30 Stratasys Ltd. Cationic polymerizable compositions and methods of use thereof
US11958233B2 (en) 2012-03-01 2024-04-16 Stratasys Ltd Cationic polymerizable compositions and methods of use thereof

Also Published As

Publication number Publication date
CA2415707A1 (fr) 2002-01-24
US6660374B2 (en) 2003-12-09
WO2002006371A3 (fr) 2002-07-25
EP1303553A2 (fr) 2003-04-23
JP2004504427A (ja) 2004-02-12
AU2001278189A1 (en) 2002-01-30
US6350792B1 (en) 2002-02-26
US20020086161A1 (en) 2002-07-04

Similar Documents

Publication Publication Date Title
US6350792B1 (en) Radiation-curable compositions and cured articles
JP3844824B2 (ja) エネルギー線硬化性エポキシ樹脂組成物、光学的立体造形用樹脂組成物及び光学的立体造形方法
JP3609128B2 (ja) 缶外面用塗料組成物
JP5019518B2 (ja) 光学的立体造形用樹脂組成物および光学的立体造形方法
JP5168860B2 (ja) 光重合性組成物
CN107300830B (zh) 一种新型光固化组合物及其应用
WO2015037431A1 (fr) Composition de résine durcissable par rayons d'énergie active, et produit durci
JP6988237B2 (ja) 紫外線硬化型組成物、２次元又は３次元の像の形成方法、硬化物、及び組成物収容容器
JP2015174929A (ja) 反応性モノマー、およびそれを用いた重合性組成物
CN109880434A (zh) 一种可固化组合物及其用途
JPH0641213A (ja) 光硬化性尿素含有組成物からテキスチャー被覆を得るための方法
CN110358353A (zh) 一种紫外光固化光纤着色墨组合物及其应用
JP2004168869A (ja) シート状光学物品用活性エネルギー線硬化性樹脂組成物及びシート状光学物品
CN111324009A (zh) 光固化组合物及其应用
CN110964374A (zh) 辐射固化组合物的防雾应用
KR20230155316A (ko) 전자기기의 강화 유리 보호용 광경화형 코팅 조성물
CN115160927A (zh) 一种紫外光涂层及其制备方法
JP2003327899A (ja) 光硬化型パテ組成物
EP4157905A1 (fr) Composition de résine photodurcissable destinée à être utilisée en stéréolithographie
CN112143284B (zh) 辐射固化型油墨及其应用
EP0483796B1 (fr) Composition à base de polyéthers, procédé pour leurs préparation et composition de résine photo durcissable
JP4356909B2 (ja) 光学的立体造形用樹脂組成物および光学的立体造形方法
GB1572039A (en) Radiation curable coating composition and method for preparation of the same
CN110964383A (zh) 一种辐射固化组合物
JP7277690B1 (ja) 光硬化性コート剤およびそれを用いてなるコート層を備える積層体

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NO NZ PL PT RO RU SD SE SG SI SK SL TJ TM TR TT TZ UA UG UZ VN YU ZA ZW

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): GH GM KE LS MW MZ SD SL SZ TZ UG ZW AM AZ BY KG KZ MD RU TJ TM AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE TR BF BJ CF CG CI CM GA GN GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
REG Reference to national code

Ref country code: DE

Ref legal event code: 8642

WWE Wipo information: entry into national phase

Ref document number: 2415707

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 2001956162

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2001278189

Country of ref document: AU

WWP Wipo information: published in national office

Ref document number: 2001956162

Country of ref document: EP

ENP Entry into the national phase

Country of ref document: RU

Kind code of ref document: A

Format of ref document f/p: F

WWW Wipo information: withdrawn in national office

Ref document number: 2001956162

Country of ref document: EP

点击 这是indexloc提供的php浏览器服务，不要输入任何密码和下载